


Just Ask

by compo67



Series: Chicago Verse [7]
Category: Supernatural
Genre: Anal Fingering, Anal Play, Anal Sex, Bottom Sam, Breathplay, Domestic Fluff, Dominant/Top Dean, Explicit Sexual Content, Felching, M/M, Multiple Orgasms, POV Dean Winchester, Rimming, Schmoop, Sex Toys, Sibling Incest, Timestamp
Language: English
Status: Completed
Published: 2013-09-10
Updated: 2013-09-10
Packaged: 2017-12-26 06:01:44
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,242
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/962453
Author URL: https://archiveofourown.org/users/compo67/pseuds/compo67
Summary: <blockquote class="userstuff">
              <p>Another fill for the SPN Kink, with some deviation. Made to be a time stamp to the Chicago Verse, so the boys are older. Original Prompt: Sam gets off a lot harder if his hole is played with. The stage in his relationship with Dean doesn't matter, it can be Dean first finding out or after they've started messing around or whatever. Basically I want a really shy and slightly mortified Sam asking for it in any way (verbal, non-verbal, Dean just knowing). They both get off on it.</p>
            </blockquote>





	Just Ask

**Author's Note:**

> This doesn't quite fill the OP's prompt but I figured I should give them credit for the idea. I love the Chicago Verse, so I basically just applied the prompt to this and made a time stamp. I also kinda got carried away and wrote more than I had intended! Oops. 
> 
> That sex shop does exist in Chicago, it's wonderful. The toy they're using is here: http://early2bedshop.com/tiger-g4-vibe.html. (NSFW link!)
> 
> Anyway, enjoy reading! Perhaps have a fan with you. Phew!
> 
> Comments and kudos are sooo appreciated! <3

 

There were a lot of things that Sam Winchester, at forty-two years of age, still wasn’t open with to his brother. And that bothered Dean.

 

They were supposed to be the cute gay couple on the block that paid their rent on time and finished each other’s sentences and knew everything about their partner. Sam knew a lot about Dean—even if most of what he knew about Dean disgusted him—and Dean knew a reasonable amount about Sam. Okay, well, for men that never grew up sharing and caring their feelings and given what they’d been through, they knew each other as well as Dean figured they could.

 

He didn’t expect to constantly know everything about Sam and vice versa. Sam still didn’t know that Dean sometimes logged onto his laptop and listened to podcasts about a small desert town. So he was sure that the Sasquatch probably had his own secret things that may or may not involve braiding his long locks of hair.

 

What really bothered him what that there were obviously things Sam wanted to try in a more… intimate aspect and he either couldn’t ask Dean or didn’t want to ask Dean. Both thoughts depressed him and opened a can of worms he preferred stayed welded shut.

 

If Dean couldn’t be what Sam always needed in terms of a partner—art shows were boring, no matter how much Dean tried—then he could at least be what Sam needed in bed. Or against the kitchen counter. Or on the sofa in the living room. Or in the shower. Okay, so they had a pretty active sex life, as far as incestuous sex lives went. They pretty much always had, even under the covers and fooling around at truck stops or corn fields or the backseat of baby. Once they knew what they could do together there was no limit. Until… the rest of the world caught up with them and… Dean was not going down that road now. Another can of worms. Who the fuck kept cans full of worms?

 

It should have bothered him more that he thought of himself as being at least capable in bed and nothing more, but that was the way he’d always thought of himself. Good, but not good enough in so many ways, so someone might as well take the good he had to give. A confusing and problematic sense of self to say the least.

 

But this wasn’t about him and his stupid self-loathing and his self-doubts; it wasn’t about him being insecure or unsure or incapable of delivering. It was about Sam.

 

The man could ask (command) Dean to attend a black tie gala and dance at least one dance with him but he couldn’t ask for something in bed. Dean considered their sex life pretty fun and interesting. He was a child of the internet, he understood what kink was, considered himself somewhat kinky and open minded. The breath play thing took a while for them to master, but eventually it was like a science. Just another aspect of fine tuning and aging well. There were a few other things that involved ropes and lace and ice cubes but Dean had to stay focused. If they could do all that, then why did Sam not want to ask for a little something more?

 

Over the past few weeks it had been obvious that Sam came harder when Dean rimmed him first, then fucked him. But Sam didn’t ask for it and tried to make it seem like it was no big deal whether Dean went down on him or not. Yet clearly, orgasms went from four star to off the charts when Dean did.

 

Usually it was Sam being all “you should be able to talk about your feelings and ask for things you want.”

 

Obviously something was hindering Sam from asking.

 

Dean hoped it was something he could fix or at least remedy.

 

So, he tried his best. He ordered Sam’s favorite mains from their regular Thai place, cracked open four beers, and put on a chick flick Dean had previously balked at being subjugated to see. When Sam arrived, he promptly asked, “Are you a shape shifter? Be honest, because I might not kill you. This is nice.”

 

Remaining focused on his mission, Dean simply assured Sam that he was not a shape shifter—fucking jerk—and grumbled for him to get his ass on the sofa before all the beers were his and the movie changed to boxing on HBO.

 

They ate and drank and Sam made stupid comments about how the movie was a reflection on self-esteem and modern technology.  They settled into their favorite couch and Dean had an arm slung around Sam’s broad shoulders, occasionally flicking or twirling a piece of Sam’s hair between his fingers. Full, buzzed, and happy, Sam’s hand was eventually down Dean’s jeans, jerking him off slowly as the movie played.

 

“Fuck yeah,” Dean grunted, spreading open his legs, giving the man some room to work. “Little lower, Sammy.”

 

Complying, Sam rested his head on Dean’s shoulder before moving his hand down. Long fingers curled around Dean’s balls. One finger rubbed at that spot just under and behind them, the spot Dean enjoyed having touched when he’d come all over Sam’s face.

 

“You’re gonna miss your movie,” Dean murmured, his voice low.

 

Sam just shrugged and kept moving his fingers. “Figure I should put out.”

 

“How considerate of you.”

 

“I try.”

 

Fifteen minutes later and they were teenagers again, breathless and moaning on the couch, clothes everywhere but on them. After making out—Sam was a fucking filthy kisser, shit—and grinding against each other, Dean got on his knees and began a wet, loud blow job. When he pushed Sam’s thighs up and aside, he felt a little bit of hesitation from Sam. He tried to go a little further, sensing that Sam had relaxed. He kept a hand stroking Sam’s cock as his mouth ventured downwards.

 

“Oh,” Sam panted and tensed up when Dean started rimming him. When Sam tensed up again, Dean stopped. He couldn’t be _that_ bad at it.

 

“Okay,” Dean huffed, wiping his mouth with the back of his palm. “What gives, Sam? You don’t like this? Should I do something else? Do I suck—don’t fucking laugh at that.” Dean didn’t consider that it might be difficult to have a serious discussion while Sam’s still hard cock was inches away from his mouth or his face in general. Dean kept his hands on Sam’s knees, waiting for an answer.

 

It confused him when he realized that Sam was _shy_.

 

His six foot five, trained in every combat weapon ever, seen the end of the world happen twice brother was fucking _shy_. Dean suppressed his big brother urge to laugh.

 

Stammering and fucking blushing, Sam did not make eye contact with Dean as he said, “Uh… n-no it’s not that… it’s not you. I just… Do I have to?” For a second, that last part sounded so innocent, so little brother-esque, so “do I have to finish my vegetables, Dean?” that he almost gave in. He could feel the, “Forget it Sammy” at his lips. But then he realized that Sam was giving him the innocent puppy treatment.

 

“Yes,” Dean barked but quickly lowered and softened his voice. “I asked you an honest question, Sam, can I get an honest answer?” He sounded so much like Sam at that moment, it was beyond odd.

 

Sensing that he had been cornered with his own logic, Sam sighed. He nudged Dean away. “Fucker. Fine.” He took a deep breath and sighed. “I… I _really_ like it when you… you do that.”

 

“Uh, okay? You have since like, forever.”

 

“No, Dean. Like, ugh. Even more now. I don’t know why. I just… dude, stop grinning! How am I supposed to tell you I want you to eat out my ass if you’re going to act like this?!”

 

At that, Dean dropped the grin, though he kept on a playful expression. “Just like that. Man, I was worried. Okay, stand up.” Dean sat back on his heels and waited. “C’mon, ain’t got all day!”

 

Sam looked at him and blinked, then stood up and faced the couch. “What? Like this?”

 

“Yeah,” Dean murmured, admiring the spread before him. He’d never been much for other dudes’ asses, but his brother was different. His brother was just… Sam. There wasn’t a part of Sam he wasn’t familiar with or grossed out by. Yeah, Dean didn’t _enjoy_ having Sam’s pubic hairs in his teeth after a blow job or touching his feet for a massage, but these were things that just happened. It was part of sex and being close to someone. Even someone like Dean Winchester knew that.

 

Besides, Sam still had the perkiest, tightest ass on the block, and as someone they once knew said, Dean could bounce a nickel off that thing. His brother was clean and familiar and asking for something that would get them both off.

 

So he started, pushing Sam on his knees so that he was kneeling on the couch, ass pushed out, legs spread. It was a source of pride that Sam allowed Dean to move him in any way he wanted.

 

“You are so fucking confident, aren’t you?” Sam snorted, chest pressed against the back of the couch.

 

“Well, when someone says, ‘eat my ass out’ I don’t exactly need a lot of direction,” Dean snipped. “This ain’t rocket science.”

 

“No but how do you know what I want? There’s eating out and then there’s… going to town.”

 

“You,” Dean muttered, poking Sam in the thigh, “are going to have to shut up for this to work.”

 

Just when Sam was going to say something else—always had to have the last word, god dammit—Dean spread his ass open and dove in. Sam wanted him to go to town, well, he’d go to fucking town. For some reason, Sam was doubting his abilities. Did Sam not _see_ the mouth Dean had? Dean Winchester considered that mouth one of his finer qualities.

 

At first, Dean’s only object was to get Sam hard again. That wasn’t a problem; Sam was soon enough grunting and groaning, cock bobbing untouched in the air, occasionally grinding against the couch. This part was pretty routine. Opening Sam up for a fuck was one of Dean’s favorite aspects of incestuous gay sex. He literally knew what Sam felt and looked like inside.

 

But rimming only lasted so long before Dean was aching to push his cock in and feel that deep burn and drag. The thought of Sam’s ass pushed down on his hips excited him. With both hands he held Sam open and tongue fucked the loosening, spit-slick, hungry hole open. It was pink and almost delicate, except Dean knew exactly how much it could take. Tongue darting in and out hungrily, Dean started to moan, making low vibrations with his mouth, pressing his lips to the hole and sucking on every third stab with his tongue. He drew this out until Sam was whining, come drooling from the tip of his cock.

 

Taking a small break, Dean shoved two fingers in, without any warning. He thanked years of experience for being able to lube up on the sly. Slick and firm, his fingers pushed into warm, tight heat. Sam keened and gasped, pushing back, grinding down. Dean steadied him and started licking the sensitive edge of Sam’s hole, where his fingers were currently in. While his fingers scissored and curled, his tongue kept lapping and poking, eventually pushing in alongside.

 

“Oh fuck,” Sam whined. “Oh shit. Dean!” When a finger pushed against Sam’s prostate, Dean saw Sam’s cock twitch. A few more deep pushes and Sam was losing it fast. Dean was surprised at how much he was enjoying this. Sure, he liked doing this for Sam, but he found himself genuinely getting off on it. How many ways could he play with Sam’s ass?

 

“Hold on, just a sec,” Dean muttered and pulled away entirely, scrambling to get to his feet and practically running to his room. He heard Sam curse him out as he dug through a drawer. Under a layer of innocent shirts were their small bounty of toys. Sam had taken him to a feminist sex toy shop—which Dean hadn’t understood the concept of, but did once he left—and they blew one of Sam’s paychecks on a bag of discreetly packaged goods. The pink-haired owner of the shop had been their personal shopping assistant, asking questions like, “Does he like his balls massaged?” as if she were asking the color of their home. But dammit that woman was a master of her craft. Dean found what he was looking for and ran back to the living room, where Sam was thankfully in the same position, though he was jerking himself off now.

 

“Stop that,” Dean ordered and got back on his knees, this time resting on some pillows. “Fuck, this is hot. I can’t believe you wouldn’t speak up.”

 

“Shut up, Dean,” his brother grumbled, long hair falling forward again as he settled back into his original position, hand off his cock. “This… it feels really good.”

 

“Yeah, I bet.” Expertly, Dean lubed up the toy and slipped the cock ring on Sam. It amused him every time that they had to get an extra-large one. He then pushed Sam’s legs open a little further and pressed the blunt tip of the toy against the waiting, hungry hole. “You take it so fucking good,” Dean purred, watching the muscle stretch and Sam’s hips falter. “Yeah baby,” he kept cooing, one hand groping and squeezing Sam’s ass. This was his favorite toy to use on Sam. It was curved and painted a dark blue, with a ring at the end Dean discovered he liked to suck on. The ridges on it made it extra special.

 

“Dean,” Sam moaned, clinging to the couch. “It’s… it’s right up on my…”

 

“I know. Deal with it.”

 

“It’s too much. Oh fuck…” Sam’s cock was throbbing and twitching in vain efforts to come. Dean made sure the ring was on securely. He wanted to see Sam’s cock bloat up.

 

Finally, he started again. He licked and lapped at the base of the toy, slurping enthusiastically, sucking on the loop handle and moaning. His own cock was hard and heavy, and a few times he had to squeeze the base to keep from coming too early. He managed to keep himself in check. Sliding it in and out a few times, watching it disappear inside Sam, and he couldn’t take it anymore. He could only put his brother through so much…and he himself was dying to come.

 

Finally, he switched it on the lowest setting, making sure the rounded head was pressed right up against Sam’s prostate. A rough cry was heard from Sam but Dean didn’t care at the moment. He started to suck off the loop handle like it was Sam’s cock, pressing his lips firm against the pink muscle. When Sam reached around and grabbed Dean’s hair, then pushed his face forward, forcing Dean’s face between his ass, Dean lost it. With his tongue, he switched the setting up, not minding the vibration in his mouth. He closed his eyes and moaned when Sam kept humping his face back against Dean’s mouth, working the toy, thighs and ass flexing and clenching.

 

“More! Dean, more, more, more, please, oh god,” Sam cried out, grinding his ass backwards. Dean readjusted himself—more so that his neck wouldn’t snap, Sam was fucking out of control—and took the cock ring off his brother. Immediately after, he cupped Sam’s ass with both hands and yanked him down roughly, groaning as he was face deep in Sam’s ass.

 

With that, Sam lost it. He came untouched, cock and balls jerking, come splattering the couch in thick ropes. He was fucking _loud_ , screaming various curses and odd phrases in Latin, coming so hard his breathing was ragged.

 

“Come inside me,” Sam pleaded, taking his hand off Dean’s head. “Dean, do it, please!”

 

He was just at the edge of coming, shit. Dean grunted and tried his best. He was only a man for fuck’s sake! He couldn’t just rip the toy out of Sam, though he eased it out as fast as he could without hurting him. As he thought, he didn’t last two minutes once his cock was inside Sam, though for that minute and a half, he fucked his brother hard and merciless against the couch, pounding his ass from the best angle. Sam was all set for another orgasm—lucky fuck—and pulled Dean’s hands to his throat. Dean groaned and felt his eyes roll. He pressed down at the proper spots and felt Sam’s heart beat speed up.

 

Dean came, buried deep, with a loud, possessive growl. As he finished, cock twitching, he bit into the meat of Sam’s neck and left a dark, angry looking mark. He felt Sam finish his last orgasm then shake and tremble against the couch, chest heaving.

 

“Ooh,” Sam moaned, his voice shot. “Dean…”

 

“Uh huh,” Dean breathed, shaking a bit himself. “Hold on.”

 

“I can’t anymore dude,” his brother whined.

 

“Yeah, yeah, I know.” Dean slid out carefully and knelt down again.

 

He sighed as he watched his come slowly leak out of Sam’s red, puffy hole. Romantic saps talked about watching sunsets together. To Dean, this was romantic. Okay, well, not romantic, but it had all the qualities of romance. Intimacy and all that shit. Tender and gentle—well, as he could be—he lapped up his come, cleaning and soothing Sam as much as possible.

 

“That feels good,” Sam purred with a sigh. “Thanks.”

 

“Yeah.”

 

It surprised Dean when Sam actually kissed him afterwards, without ordering Dean to wash his mouth out. It was a simple, sweet kind of kiss.

 

“My jaw fucking hurts,” Dean complained after a moment of silence. He received an elbow to the ribs. They lay on the couch, limbs and all tangled together. The movie had been over a while ago, but Sam lazily reached for the remote and started it over.

 

“Sometimes,” Sam whispered, arms over Dean, “I just… this doesn’t seem real.”

 

He wanted to make a joke or brush Sam off, but that hit too close to home. He had figured out what was bothering Sam, what he had wanted, and given it to him freely, no expectations or requirements necessary. They didn’t have to know everything about each other, but Dean had realized when they bought this house, when they arrived in Chicago, that they did have to talk to each other. They did have to work at being Sam and Dean, as much as he hadn’t wanted to admit that when he was younger.

 

Everything concerning Sam seemed, to Dean, so effortless, so easy. But Sam as a person was not effortless or easy to figure out or understand.

 

So, while he wanted to crack some lewd comment about how real his dick was, or how he’d fuck Sam into a mattress even in his dreams, Dean refrained.

 

Instead, he settled in, letting Sam be the big spoon for once, and put his hand over Sam’s.

 

Simply, he replied, “This is real, Sammy.”

 

 

 

 


End file.
